PayIt gains $25M follow-on investment from early backer Weatherford Capital
May 31, 2019 | Tommy Felts
A Tampa-based venture capital firm run by three brothers sees investing in Kansas City’s PayIt as part of its long-term strategy.
Weatherford Capital first backed PayIt in 2016, through a $4.5 million Series A round led by New York-based Advantage Capital Partners, and followed by Weatherford, Royal Street Ventures, the Missouri Technology Corporation and Five Elms Capital.
The firm confirmed to Startland this week a follow-on investment of $25 million for the Kansas City GovTech innovator, which is led by co-founders John Thomson and Michael Plunkett.
Specializing in GovTech applications that better connect government to its constituents, PayIt made news in 2018 thanks to major partnerships with the State of Kansas and the Unified Government of Kansas City, Kansas. Its iKan app notably allows Kansas to skip the line at the Department of Motor Vehicles.
PayIt was named one of Startland’s 10 Kansas City Startups to Watch in 2017 and 2018.
“As investors, we seek out quality teams, leaders, and healthy cultures, not just assets and good ideas,” reads the investment firm’s website. “We believe that through long-term partnerships with purposeful capital and high-quality companies we will produce outcomes that promote human flourishing.”
Driven by Will, Sam, and Drew Weatherford, the firm has a nationwide focus on middle market firms with enterprise value of $50 million or more.
In March, PayIt made headlines with a more than $100 million investment by New York-based Insight Partners, which provided an exit for investors within the KCRise Fund.
Click here to read about the game-changing investment for PayIt and Kansas City.
“The company [PayIt] happens to be in Kansas City — Investors expect a return. They’re looking for big, scalable, durable businesses,” PayIt’s Thomson said at Startland’s May Innovation Exchange event. “You’ll hear the phrase ‘escape velocity’ — those that can turn into the next Fortune 500 company in a market or a category. It’s all about the execution of the business, the growth trajectory and how investable is that team and business.”
Meeting with more than 85 firms in its most recent funding push, however, PayIt saw rising interest not only in its GovTech offering, but in its hometown backing, he acknowledged.
“There’s a broad awareness of Kansas City, this ecosystem and this environment — and that it’s been on the rise,” Thomson said.
Featured Business

2019 Startups to Watch
stats here
Related Posts on Startland News
How KC transformed entrepreneurship from counterculture into a model for the mainstream
Veteran ecosystem builders returned to the Heartland this week, urging a new generation of entrepreneur advocates to embrace Kansas City’s style of experimentation and its uniquely collaborative startup culture. “Entrepreneurship is not spreadsheets and business plans,” said Jonathan Ortmans, who founded the Global Entrepreneurship Network (GEN) — the nonprofit parent of Global Entrepreneurship Week —…
They didn’t want to go corporate; how AI gave brothers the tools to forge their own path, together
Tyler and Garrett Amundsen are using AI to help insurance brokers spend more time on relationships and less time on data, the duo shared. Inspired by conversations around their family’s Kansas City dinner table, as well as the latest tech developments, the brothers launched LightDoc in early 2023 to automate and streamline repetitive tasks that…
He retired after an exit; now this govtech veteran is back in a CFO role for KC-scaled PayIt
As Kansas City-built PayIt scales across North America, a new financial leader is expected to help guide the company in its game-changing efforts to help government agencies modernize, serve their residents, and improve operating efficiency. Steve Kovzan, a nearly 30-year veteran of leadership across government technology and finance spaces, is now chief financial officer at…
KC Tech Council celebrates tax fix in Trump’s ‘One Big Beautiful Bill’ that boosts growing businesses
A tax fix included in the recently signed “One Big Beautiful Bill” — sprawling legislation meant to overhaul taxes in the United States — marks a major win for Kansas City’s tech and innovation economy, said Kara Lowe. At issue: a long-awaited change to Section 174 research and development expensing that now allows businesses to…

